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Using ChemDraw for iPad and Flick-to-Share to Increase Engagement in Organic Chemistry

Layne Morsch

November 18, 2013 - November 20, 2013

Abstract:

During my summer course, I began to integrate ChemDraw for iPad into my undergraduate organic chemistry lecture. There was an obvious increase in classroom participation and engagement with the material as a result. I will show the types of problems students worked on in class and model how Flick-to-Share works to exchange information. Successes and difficulties in integrating ChemDraw for iPad into the course will be discussed as well as how some difficulties have been addressed and future development needs.

Using ChemDraw for iPad and Flick-to-Share to Increase Engagement in Organic Chemistry

My organic course, teaching from iPad

I began teaching from an iPad during Fall semester 2012 for my organic chemistry 1 course. I wrote on the iPad similarly to using the whiteboards while using Airserver to connect to the computer in the room and projecting onto a screen so the class could follow along. I use Camtasia Relay to record the screen and a room microphone to record what I am saying as well as any class discussion. These lectures are then posted on Blackboard for students to watch back while studying.

Drawing and Flick

ChemDraw for iPad can be used to draw nearly all chemical interactions I use in organic chemistry, from reactions and mechanisms, to stereochemistry via wedges, sawhorses, Newman projections, Fischer projections and Haworth projections as well as molecular orbitals. Flick-to-Share can be used to send any of these drawings in real time to other users that have been added as contacts. It can also be used to share with a group of contacts at once, where one flick can send the material to a number of users, which is ideal for in-class use.

During spring of 2013, I was contacted by McGraw-Hill Education about pilot testing the new ChemDraw for iPad that would be released by PerkinElmer during the summer of 2013. I was immediately interested in finding ways to help our students become more familiar with ChemDraw as I felt it was being under-used on our campus. PerkinElmer lent 25 iPads for my summer organic chemistry students to be able to take with them for the entire course. This allowed them to work on ChemDraw for iPad outside of class time and become more familiar with using the app.

As I prepared to use ChemDraw in class, I considered what it could be used for. In addition to the students becoming more familiar with ChemDraw, I immediately saw the value in the imbedded Flick-to-Share functionality. This allows people to easily exchange their drawings with others by simply flicking the drawing to another user’s ID. During most class periods, I used this to flick a problem out to the students and have them flick their answers back to me. Since I began teaching from the iPad, I have been walking around the room while I am teaching, and I noticed that when I give students a problem to work on during class that 1/3 to ½ of the class did not attempt the problem, but simply waited until I later solved the problem to write anything down. To me, this defeated the pedagogical purpose of giving in-class problems, which is to help students determine if they understand how to apply the concepts we are discussing. If students attempt to solve a problem and get it right, it shows they have a good understanding, while if they try and get it wrong, it shows they need to spend more time studying the material outside of class. If they wait for me to solve the problem they have missed this opportunity to self-assess. By using ChemDraw and Flick-to-Share, I was able to get all the students in class to engage with the problem-solving by giving daily points for sending me answers via Flick. I felt it was important not to penalize students for giving wrong answers, as I believed that engaging with the problems would encourage self-assessment, therefore I gave students points whether their answers were correct or not.

Fig. 1 An example of an in-class problem. The black drawings were flicked to the class, the red is an example student response.

There are many types of problems that I have been able to use ChemDraw for iPad to have students solve during class including:

Draw a structure with 5 or more carbons that would be water soluble

Draw a resonance structure of a given molecule

Draw the enantiomer or diastereomers of a given structure

Draw the product(s) of a reaction

Draw the mechanism of a reaction

Draw all the Newman projections for a molecule and label the highest and lowest energy conformations

Draw both chair conformations for a substituted cyclohexane and label the lowest energy conformation

One unexpected outcome I found while walking around the room as students worked on their problems was that I could quickly identify mistakes being made in mechanisms and structures. I attribute this to the more standardized nature of drawing with ChemDraw than drawing by hand. This has led to being able to correct these mistakes as they are happening during class.

Fig. 2 A common error drawing E2 reactions without having the base remove the proton alpha to the leaving halogen: ChemDraw for iPad allowed me to quickly show why this mechanism pathway is not possible.

I also experimented with using ChemDraw on two exams during the summer. I flicked partial reactions to the students and asked them to answer the problems and flick the responses to me. I required them to complete this part of the exams before handing out the paper portion as ChemDraw could be used to answer some of the other exam questions (such as configuration of stereocenters, as stereochemical labeling can be turned on or off on each user’s ChemDraw app). This worked well for the early exams before the students were told that it was possible for them to flick to each other (at the time, they only knew they could flick to me as the instructor). I did not have the students use the app on the final exam for this reason.

Fig. 3 Average student responses to questions relating to their use of ChemDraw for iPad during summer courses at UIS and SLU. The scores were on a 7 point Likert scale with 1=low and 7=high, SLU n=21, UIS n=7.

Student evaluation

PerkinElmer sent a user interface and usability expert, Jennifer McCormick from User Experience, to run a focus group with the students from my summer class. She used a combination of survey and interviews to assess student attitudes toward the use of ChemDraw for iPad. McGraw-Hill Education sent Patrick Diller to do the same, but to assess the educational aspects of using the app in class. The feedback from these two sessions was very important in increasing the usability of ChemDraw for iPad in the classroom. The low score for ease of sharing structures at UIS had two easily identifiable reasons. First, group flicks were not yet possible, which meant that I had to flick everything individually to each student in class. This functionality was added to Flick-to-Share in a subsequent update. This low sharing score also helped us to identify that the students wanted to use the app outside of class while studying with each other and wished they could flick drawings to one another. After learning this, I immediately told the students that they could flick to each other and showed them how to do so. In hindsight, I feel that students use of their iPads while studying is much more valuable than using it on exams (which is the reason I had not told them they could flick to one another). The comments relating to ease of drawing structures showed that many students (as well as the instructors, though we were not included in the survey data) desired a text tool that would allow for labeling of items on the drawings. This was also subsequently added to ChemDraw for iPad along with chair, Newman and Fischer structure templates all of which have expanded the usability of the app. Many of the comments relating to overall satisfaction or perceived usefulness related to the awkwardness of switching between writing notes on paper and using the iPad for problem solving.

Future developments

The main element that would improve the classroom usefulness of ChemDraw for iPad would be a way to integrate with some type of class response program. This would allow for immediate analysis of responses which would aid instructors in identifying and correcting misconceptions during class.

Conclusion

ChemDraw for iPad has been used to increase engagement during organic chemistry lectures by utilizing Flick-to-Shareto send out problems and receive answers from the students. There have been several improvements in the usability of ChemDraw for iPad since the summer pilot that make it more versatile and have fixed some of the main issues students experienced. I am continuing to use it with a larger class and will again survey this class to determine how the improvements will affect student attitudes and engagement.

Acknowledgements

This work has been supported by PerkinElmer with special recognition to Hans Keil and Phil McHale for their oversight of the pilot studies. Patrick Diller at McGraw-Hill Education for insight into pedagogical developments relating ChemDraw for iPad to teaching and survey data. Jennifer McCormick from User Experience for survey creation and implementation. Dr. Michael Lewis of Saint Louis University who also participated in the pilot study with his 2013 summer organic chemistry course.

Comments

I was really impressed with the iPad drawing app. It all looked so easy (at least for the expert).

You have mentioned a couple of times that your students make mistakes drawing the arrows in the wrong direction.Have you explored this any further to get an idea of why this is so?

Do they not understand the direction of the arrow convention? from nucleophile to electrophile?Or is the problem more fundamental in that they do not understand which species is the nucleophile and which is the electrophile?

We assume heaps of prior knowledge when we draw arrows (location of non-bonding electron pairs, the effect of electronegativity on the availability of these, bond polarity, formal charge, etc etc). I have data collected from our first year students in the context of organic mechanisms that indicates a disturbing lack of understanding with respect to the location of non-bonding electron pairs and bond polarity. On the other hand our data indicates that once the barrier of identifying nucleophile and electrophile has been overcome, they have little problem deciding on the arrow direction.

Do you do any work in class asking students to add non-bonding pairs to their structures in ChemDraw?

In order to remind the students of electron distribution, is there a possibility on the ChemDraw app to expose the potential density surface?That would be something that can't be done on pen and paper. I guess that I also have the worry that just asking students to draw structures is not much of an advance on getting them all to draw them on a piece of paper and you circulating throughout the class. My feeling is that the use of technology is justified only IF it adds value.

Also you mentioned that the tools you need have not yet been developed. What tools do you think that you need?

Thanks for the insight into arrow drawing problems. I often try to remind students how many layers of knowledge they are using to solve problems later in the course and into organic 2. I also really like your idea about having them draw in non-bonding pairs (especially when they use those electrons in a mechanism). I would say that my students that are struggling are the ones having difficulty with electrophile/nucleophile. In my class I ask them "who has electrons and who wants them" for nearly every reaction. I am often surprised that some of the students cannot answer this question even in the 12th week of the semester. Unfortunately without using any class response system it is difficult to gauge how many students do not understand as there are many students that will answer if I ask the questions verbally.

Chem3D can be used to model electrostatic potential maps, but not on the Chem3D iPad app. This type of calculation is a bit more advanced.

I completely agree with your assessment that technology is only justified if it is adding value. The value I have seen and tried to stress through the paper is student engagement. My goal is to get all the students solving problems and trying to apply the concepts they have been learning. The Flick-to-Share part of ChemDraw for iPad has allowed me to do that, though there are real-time limitations. Even with my relatively modest-sized class of 60 for organic, I don't have time to go over the student responses during class to really understand what the students know and what they are struggling with. This is what I was alluding to when I said the tools are not yet available to do what I want. More clearly, I want students to be able to draw reactions and mechanisms during class the results of which will be available to me in some form of data that shows how many have it right or wrong and even better, what the errors are and how common they are. If, in addition to this, the technology could group the students by location and a mix of right and wrong answers for discussions (like Learning Catalytics does) that would be amazing for an interactive organic chemistry learning environment.

This question concerns your experience with using ChemDraw on two of the exams, and I was wondering if you could comment to the list on your experience. I am more interested in thoughts towards best-practices with respect to giving part of an exam on computer and part on paper. Clearly different students will show different aptitudes with the technology, and those who are not digitally native may need more time to navigate through the computer part. This means they have less time to finish the rest of the exam, which might skewer the grades in favor of students who are more comfortable with technology.

But there is another facet that has nothing to do with technology, in that when taking an exam I advise students not to get bogged down on difficult problems if that means they run out of time to finish the exam, and if there is a question they did not understand, to move on and go back to it once they have completed all the questions. That is, it is better to answer what they know, and not leave half the exam blank because they were stumped on one question. If that "dreaded question" was on the ChemDraw part of the exam, and they had to turn that in before starting the rest of the exam, that student would be at a disadvantage to another student, whose “dreaded question” was on a the pencil/paper part of the exam.

I have seen this problem myself when I administered lab finals where in part of the final students identified virtual unknowns, and the rest was paper and pencil. Initially, I administered the Virtual Lab part first, and although all students had done virtual prelab and postlab activities, some were more comfortable using technology than others, and clearly got more time to do the paper and pencil part, and I realized I had a problem. The best solution I came up with was to administer the two parts of the exam at different times. Unfortunately, that is not always possible, and when they have to be in the same period, I now have the students do the virtual part last. But there are issues with that, in that I need to transition the students to the virtual part early enough for them to be able to complete it.

I would like to know if you, or anyone else, have an alternative technique or suggestion for administering exams involving both computer and pencil/paper components within a single period.

Let me start by being honest. I didn't consider all ramifications of including ChemDraw on the exam in advance, I mostly was trying to test the boundaries of what could be done and tried to come up with different ways to use the iPads. That being said, one advantage of testing this in the summer is that my class was 2.5 hours long. This allowed me to tell students they could take as long as they want on the ChemDraw and that I wouldn't start the 1 hour for the exam until after they submitted their ChemDraw responses. Also, I don't think I put any "killer" questions on ChemDraw, on one exam I asked them to draw SN1 and SN2 mechanisms (well, I didn't label them as such, I gave them reagents that would follow those mechanisms). Though I didn't do any data analysis on the results of the ChemDraw responses vs. standard drawing responses, what I saw was typical for mistakes that students make (for example, drawing arrows the wrong direction and not determining the proper mechanism).

I don't have any further experience with the test paradigm as there currently is no way to "lock down" the flicks for a period of time to avoid the students sharing with each other during an exam. This is also not one of the features I am campaigning for. I am much more interested in a way to get immediate classroom feedback (like clickers, learning catalytics, etc) to be able to incorporate ChemDraw for iPad to improve classroom engagement and assessment.

Prof. Morsch, thanks for sharing your experiences. It indeed seems to be a great way to communicate on chemical structures and processes. Is the industry using such tools?

Did you come across any disadvantages of this approach? Especially something that the student will fail to get? I have used the free tool BKChem to teach, but without the Flick tool (I used a projector). In my case it was not a problem because I was not teaching them Chemistry but Cheminformatics. But when I interacted with Chemistry teachers, and suggested that they use it to teach Chemistry, they weighed the pros and cons and decided against it. Their reasoning was that the students were likely to get distracted by the novelty of the tools (the year was 2007. The place was Mumbai, India. The students were studying for their B.Sc. degree).

A more serious problem was revealed when I saw how a Chemistry interviewer/examiner judged the basic Organic Chemistry abilities. It involved judging the fluency of drawing structures by hand, and how, for example, the student would draw a simple benzene ring. He then pointed out to me that if they had not seen their teacher draw on the board, they would not be able to do so themselves, because diagrams in a book don't show how a structure was drawn. Similarly, in tools such as ChemDraw or BKChem, the structure "appears" as a unit, and if the student's study was based totally on such a tool he or she would not be able to draw it fluently.

That was six years ago, and in India... the industry was not much into using drawing tools outside of some departments. The situation might have changed now. But still, would students taught through tools lose the ability to draw fluently what they have in mind? And would such a handicap hamper their careers today?

I think that the iPad app version of ChemDraw is so new (only out since the summer) that I wouldn't say it is being used a lot in industry yet. I do know that PerkinElmer has met with at least some of the companies that are big ChemDraw, E-Notebook and Spotfire users to show them how they could add ChemDraw for iPad. Also, since the tools are the same on the app version as some of the tools on the full version it makes working on the PC versions of ChemDraw easier for my students. I have an informatics lab that I teach in organic chemistry 1 where we use ChemDraw on laptops and the students are much more familiar with how to draw since they've been using ChemDraw for iPad, I really don't need to lecture on it at all.

About the potential drawing issue. I still model both when I lecture. I write most of my lecture notes on my iPad using Notability, including drawing chemical structures, reactions and mechanisms. Then we will switch to the iPad to work out a problem that I want them to send to me. I really like this mix that teaches them both how to draw by hand and how to draw using ChemDraw. Incidentally, the importance of knowing how to draw structures for themselves is why I have never used powerpoint to lecture in organic chem. I can see its uses in other areas, but the process of drawing (especially mechanisms) is vital for understanding organic chem (from my viewpoint).

My comment revolves around the used of the flipped learning environment with the idea of imbedding the flick-to-share as one of the main purposes of class time. You mentioned that one of the "awkwardness" points of the implementation was swithcing back and forth between the iPads and taking notes. My thought in overcoming this dilemma would be to take the "notes" out of the class room routine, which is where the flipped learning model comes in.

More importantly, I could definitely see the benefit in grouping students into small groups for peer-to-peer instruction where each group could be "flicked" a different problem to work on in class. If you are getting synchronous updates of students progress, you could easily adjust the level of difficulty per group or stop the class and review a missing concept. Further, grouping could be done similar to the learning catalytics approach where the students are grouped based on a response to an initial question. Giving the initial grouping, an appropriate leveled question could be assigned to each group and the groups are determined on ability rather than "friends". Further, if the problems are abled to be archived from all the groups, it would be an easy way to establish a review.

So, my question really boils down to this: Given the success that you initially had, have you considered making your class time more devoted to the application of knowledge through ChemDraw and flick-to-share or does the of acquisition knowledge (lecture/notes) trump it?

Your suggestions fit with exactly where I am right now. I like how prerecorded lectures to watch outside of class can help students to learn organic chemistry that are intelligent, but with their learning styles they need to watch an explanation a few times rather than the one time they get to see it during lecture.

I will be flipping my class beginning next semester and I agree that it should eliminate that switching back and forth between note-taking and problem solving. I was greatly challenged this fall when Dr. Matthew Stoltzfus from Ohio State University (who presented with you last fall in the newsletter here on flipped classroom http://www.ccce.divched.org/P5Fall2012CCCENL) asked me "What is the best use of my face time with students?" I am convinced that it is not giving static explanations but it could be discussion of material and problem solving. Another professor this fall asked me "What is the hardest thing we ask students to do?" My answer was solve complex problems, but the issue is that they are mostly doing this alone, often late at night, without access to the expert that could help them. With a flipped model, I can ask them to do the easier task of taking notes or seeing for the first time how a mechanism works outside of class and then work on how to apply that knowledge during class.

I have experimented with Learning Catalytics and if ChemDraw could be integrated into this system or something like it, I would love to use that in my organic classes. I feel like there is great potential to increase engagement in organic chemistry courses, but all the tools that I would like to use have not been developed yet. I will have to experiment this spring to see how to engage individuals and groups with the current tools that are available, but would love to have more converstations about how to do this effectively.

since this system allows both a student-to-student and student-to-instructor transfer of student answers, how did each affect the class? Was there a preference by students? Also, in terms of the use of clickers to gauge student progress, were you able to glance through student answers and adapt the class to the responses you saw? Since ChemDraw standardized the drawings, as you indicated, can it provide histograms of student responses?

I haven't used the peer-to-peer in class yet, though I would like to try to next semester with my "flipped" organic 2 course. I've told them about the peer-to-peer so that they can use it with each other when studying, though by informal assessment not many of them are doing so (only 14 of my 50 students have their own iPads).

There is currently no way to get histograms of student responses, but I am talking with PerkinElmer and other parties to try to encourage this capability as soon as possible. With the type of comparator that exists already with the web version of ChemDraw that is incorporated into Connect for organic courses (from McGraw Hill Education) it would be possible to incorporate some kind of "real-time" assessment. This is exactly what I want for my classes and what I am advocating for organic chemistry instruction. Once this is possible, I would find it much more useful than a clicker that is limited in the types of responses that are possible for students. I would like to be able to ask a student to draw a complete mechanism rather than select from a set of pre-drawn mechanisms which is the correct one.

I am sure that chemdraw can facilitate learning organic chemistry. Can student flicker their solutions as movies? It could be a good way to detect mistakes like the one you saw in class while drawing the elimination mechanism and not only the final response.

Thanks for sharing your experience. Could you share with us challenges that you had to face?

I like the idea of being able to flick as movies, there is nothing currently built into ChemDraw that tracks order of drawings that I am aware of, though PerkinElmer has been in contact with developers of several other apps about potential for integration, so perhaps this would be something to look into.

Challenges:

The first challenge is that using any technology like this slows down my lecture pace by requiring class time to instruct on the technology use. I plan to start "flipping" my organic classes in January where the lecture material will be pre-recorded and in class we will be working problems and discussing questions on the material, so that my alleviate some of the problem of getting behind the syllabus on material coverage.

Another challenge that I am currently facing goes back to getting the students to engage. As I mentioned, I have been giving points for trying to answer even if the answer was not correct. What that has led to is some of the students not attempting to answer during the time I give them. Instead, they were again waiting for me to answer it, then draw those answers in ChemDraw for iPad then flick me what is essentially my own answer. Last week in class, I had to announce that I will only give credit to answers flicked to me before I go over the answer with the class and only if an attempt was made to answer the problem.

Another challenge that I will be probing this semester is that the majority of my class are using a "borrowed" iPad that the IT department brings for my class each day. This means that they have no chance to practice using the ChemDraw app outside of class time, to study, to draw reactions for lab reports or any other purpose.

Thank you for sharing this very interesting paper and excellent videos on the use of ChemDraw and Flick-to-Share in your organic chemistry class.

What do you think are the fundamental differences in doing your assignments when using the ChemDraw app. vs. pencil and paper? What I am seeking your thoughts on is general and applicable to any app, in that the technology is going to introduce a bit of scaffolding through the user interface. That is, you are confined to use the features of the app in performing that activity desired, and those features must allow you to perform the task. Therefor, those features could be “narrowing down” your options for false solutions and sort of guiding you through the activity. Do you have a bearing on common mistakes, and was the nature of the mistakes different for students using the app, vs. other classes in the past which did not use the app?

I also have a question on Flick-to-Share, is it done via something like Blue tooth, or over the internet? What I am really asking, is can students do it from remote locations, or do they need to be near you (in the class room).

First, Common Mistakes: I am generally seeing the same types of mistakes that students make on paper. Many of my flick questions ask students to draw mechanisms and students will draw arrows the wrong direction, form carbocations at the wrong carbon or remove the wrong proton in an elimination. In drawing stereoisomers, students need to know what enantiomers and diasteromers are or they will draw the wrong structure. There are some mistakes that the software will identify (primarily if one draws too many bonds to an atom). Also, ChemDraw for iPad will autolabel stereocenters as R or S and alkenes as E or Z, so those types of questions cannot be asked in class using the app. (However, this can be helpful for students to practice as they can draw a molecule and decide if it is R or S, then turn labeling on and check their answer).

Flick-to-Share uses the internet to share molecules. I have actually thought that this could be used for online courses as well since students from anywhere that are part of your network can receive flicks and send responses.

It seems that there needs to be some type of database to manage the files if multiple answers are concurrently being submitted to the instructor. Is it using a cloud service? Are the images "stored" or do the students have to have their app on when it is flicked? If they are stored, where is the database? Do you need to set up accounts? Can you access the flicked files on a non-iPad device, like a windows platform? (I realize you may not be able to flick them, but can you read them?) Must this be done synchronously, or can it be done asynchronously? Can you flick a problem before class to have the students prep on?

I think I can answer most of this, though PerkinElmer may be required to answer the more complex issues on hosting. The files are stored and can be accessed from a website. On this site you can view flicks you have sent as well as received. You can sort received flicks by date, title or email of sender. You can add contacts and create groups. The stored files are CDXML which should be able to be opened by any version of ChemDraw (at least any that I have tried which includes Windows and iPad). Just like any iPad alerts, students will be able to see the last several flicks sent to them when they open ChemDraw on their iPad. They will receive a message that says "lmorsch shared a file with you". PE would have to answer where is the database, but it is not local, they run it. Each user needs to set up a free account for Flick-to-Share.

The flicks work well with synchronous or asynchronous applications, however my current limitation is that all my students do not have iPads or ChemDraw on their personal computers. This limits my ability to engage my class with flicks outside of class time. I would like to be able to have iPads for every student in my class for this reason, but that is not yet the case. Also, the Flick website is not easy to find for users if they don't know about it. I'm pretty sure that none of my students have ever used it, though they could to review material from class. That would be another way to allow students more interaction, but would again require them to have their own iPads or to have ChemDraw installed on their computers.

These are definitely good questions and I have contemplated them as well. I can address a couple of issues with the data and one possible outcome that was seen. I used ChemDraw for iPad and Flick-to-Share in a summer class with 16 students and did not have a control group to compare against. The grade distribution and exam scores were typical for this course (I have taught the same course at UIS 5 times in the summer). However, I see variance in performance depending on the group of students each year, so without a randomized control group it is hard to prove interventions are having the desired effect.

Dr. Lewis did see some interesting results at Saint Louis University. He taught both Organic 1 and 2 during the summer. The students did not have ChemDraw for iPad in organic 1, but used it in organic 2. His observation was that stronger students improved their grade in organic 2 compared to organic 1 (This was true for 8 students (class size 30) that achieved B grades in organic 1). Dr. Lewis stated that this rarely happens as organic 2 is more difficult, students typically do worse in the second semester in his classes. The poor students still struggled and there were more failing grades than in organic 1.

I will be looking at results again after fall semester, but I have also made other changes to my class (shifting to an ebook and using online homework and quizzes) so I will not have clear data-driven results for the effectiveness of ChemDraw and Flick-to-Share as an intervention.